Synthesis and thermolysis of hexacoordinate 1,2-oxaphosphetanides

被引:26
作者
Kawashima, T
Watanabe, K
Okazaki, R
机构
[1] Department of Chemistry, Graduate School of Science, University of Tokyo, Tokyo 113, 7-3-1 Hongo, Bunkyo-ku
关键词
D O I
10.1016/S0040-4039(96)02369-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Hydroxyalkylphosphoranes containing two Martin ligands were prepared by reduction of the corresponding phenylthiomethylphosphorane with lithium naphthalenide, followed by the reaction with carbonyl compounds. Treatment of the beta-hydroxyalkylphosphoranes with KH in the presence of 18-crown-6 gave a mixture of stereoisomers of the corresponding hexacoordinate 1,2-oxaphosphetanides stable in solution at room temperature. Upon heating, the adducts of benzophenone derivatives gave the corresponding benzophenones, while a hexafluoroacetone adduct afforded the corresponding olefin. (C) 1997, Elsevier Science Ltd. All rights reserved.
引用
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页码:551 / 554
页数:4
相关论文
共 21 条
[1]  
Ager D.J., 1990, ORGANIC REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01
[2]   Reactivity of carbon anions alpha to pentacoordinated phosphorus: Spirooxyphosphoranyl C-anions as valuable intermediates in olefination chemistry [J].
Bojin, ML ;
Barkallah, S ;
Evans, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1549-1550
[3]  
FREIDE JJH, 1980, J CHEM SOC CHEM COMM, P934
[4]   NEW REAGENTS .24. NEW POSSIBLE APPLICATIONS OF HEAVY MAIN-GROUP ELEMENTS IN ORGANIC-SYNTHESIS [J].
KAUFFMANN, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (06) :410-429
[5]   SYNTHESIS, STRUCTURE, AND THERMOLYSIS OF A 1,5-DIOXA-4-LAMBDA(5)-PHOSPHASPIRO[3.3]HEPTANE - A NOVEL PENTACOORDINATE 1,2-OXAPHOSPHETANE [J].
KAWASHIMA, T ;
TAKAMI, H ;
OKAZAKI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4509-4510
[6]   SYNTHESIS AND THERMOLYSIS OF TETRACOORDINATE 1,2-OXAPHOSPHETANES STABILIZED BY STERIC PROTECTION [J].
KAWASHIMA, T ;
TAKAMI, H ;
OKAZAKI, R .
CHEMISTRY LETTERS, 1994, (08) :1487-1490
[7]   INTRAMOLECULAR DEHYDRATION OF BETA-HYDROXYALKYLPHOSPHONIC ACID MONOESTERS - A NOVEL TYPE OF OLEFIN FORMATION [J].
KAWASHIMA, T ;
NAKAMURA, M ;
NAKAJO, A ;
INAMOTO, N .
CHEMISTRY LETTERS, 1994, (08) :1483-1486
[8]   SYNTHESIS, STRUCTURE, AND THERMOLYSIS OF A TETRACOORDINATE 1,2-OXABORETANIDE - AN INTERMEDIATE OF THE BORON-WITTIG REACTION UNDER BASIC CONDITIONS [J].
KAWASHIMA, T ;
YAMASHITA, N ;
OKAZAKI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :6142-6143
[9]   CRYSTAL-STRUCTURE AND REACTIVITY OF A PENTACOORDINATE 1,2-OXASTANNETANIDE - AN INTERMEDIATE OF THE TIN-PETERSON REACTION [J].
KAWASHIMA, T ;
IWAMA, N ;
OKAZAKI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2507-2508
[10]   Synthesis, structure, and thermolysis of N-apical 1,2 lambda(5)-azaphosphetidines with a pentacoordinate P center and the first observation of their N-equatorial pseudorotamers [J].
Kawashima, T ;
Soda, T ;
Okazaki, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (10) :1096-1098